A while back, I wrote about Anti-Workflow Apps -- apps that solve problems for you without forcing you to adopt a workflow that you may never fully be able to adopt.  Workflow apps (CRMs, to-do lists, project management tools) are super hard to drive adoption towards, as everyone works differently and really resists this kind of change.  (of course, it's possible when the reward is super good -- e.g., slack and git/github -- bit those times are rare and more often than that an attempted re-workflow goes splat) So I've been on the lookout for Anti-Workflow tools.  Solutions that solve a problem that you think requires a new workflow, but may actually be more effectively solved another, more clever way Today I want to talk about to-dos, because I seem to have found my own personal anti-workflow solution. I've always struggled with to-dos -- I've used every to-do management tool on earth, and have never been able to adopt a workable, effective system.  I've tried everything from complicated tracking systems like OmniFocus to simple to-do lists of every possible flavor.  Nothing has stuck.  For years and years, I kept trying, trying and trying again. In the end, I just gave up and said, fuck it, I'm not using a to-do list anymore. Not going to even try. What happened was that I ended up keeping track of my priorities in a totally different way -- a way that was actually more in tune with my existing workflows.  One part of the solution was pretty obvious, and one was surprising. On the obvious side: the calendar.  For things that I absolutely must do, and that require dedicated time, I just use my calendar.  I'm in my calendar all day long, so it's the perfect place to block out time for important things.  So now I set calendar entries for myself, to make sure I set aside time for things that need focus. The calendar is good for things I know I need to do, and that I know are important.  What it's not good for is capturing notes, ideas, and small to dos, which often just need to be captured in the moment and prioritized & dealt with (or not) later.  This is the use case that has always drawn me back to to-do apps, to no avail. In particular, the really bad thing about a to-do list for this use case is that all it does is make you feel guilty.  Items get added to the list, and whether you really need to do them or not, you feel drawn to.  And then when it doesn't happen the to-do list just becomes a giant pile of guilt that you do your best to ignore (that's what happens to me at least). That brings us to the less obvious solution.  What I've found is that a great way to handle both the capture / prioritization issue and the guilt issue is to use a Sparkfile.  Long time readers will know that this blog is named after my favorite idea from Steven Johnson's Where Good Ideas Come From: the "slow hunch" approach to developing ideas.  Another idea from that book -- unearthed by studying epic thinkers of the past like Darwin and DaVinci -- is the Sparkfile: a long, running list of thoughts & ideas.  Fragments that pile on one another over time. One way to cultivate the slow hunch is not only to keep a sparkfile (in addition to other kinds of journals), but to constantly pour back through it re-reading and reconsidering your previous thoughts, ideas and observations. Turns out that this is also a pretty good way to filter inbound ideas of things to do.  Just add them to the spark file, continually review the list, and occasionally do things (immediately or via calendar), and then add new stuff to the top as you think of more things.  No pressure -- and absolutely no expectation -- to do everything on the list or turn it into a perfect set of priorities.  Just let the mind run, capturing as you go. For me, this idea ties back into anti-workflow because I've been keeping a personal blog/journal for about 7 years now.  Which was in many ways a sparkfile, though it started out slightly more long form (starting with a private wordpress blog).  The big revolution happened last fall, when I switched over to using Diaro.  Diaro is a personal journal tool, with both a desktop web client as well as a mobile app.  The mobile app is the key, as it makes it possible to really quickly jot down a thought -- as quickly as you'd do on a to-do app, or email, or notepad. So in the end, the solution to my to-do workflow was not to add a new to-do workflow.  Rather, it was to extend the workflows I already had going, calendars and the sparkfile.  Boy it feels good.

I couldn't sleep last night, and was up around 4am lurking on Twitter.  I came across an old friend, Elizabeth Green, who is an accomplished and awesome education writer -- you've probably read some of her recent NYT mag cover stories, and it turns out she has a new book out, Building a Better Teacher.  I know Elizabeth because back in 2008 at OpenPlans, we worked with her to launch GothamSchools, which eventually spun-out and became Chalkbeat. I said to myself: oh yeah, that was such a great project; I had totally forgotten about that. So awesome that it is still up and running and thriving.  And I dutifully headed over to update my Linkedin profile and add it to the section about my time at OpenPlans. During my nearly 6 years at OpenPlans, we built a lot of great things and accomplished a lot, and I'm really proud of my time there.  But it's also true that we made a ton of mistakes and invested time, money and energy in many projects that ranged from mild disappointment to total clusterfuck. Looking at my LinkedIn profile, I started to feel bad that I was only listing the projects that worked - the ones that I'm proud of.  And that's kind of lame.  The ones that didn't work were equally important -- perhaps more so, for all the hard lessons I learned through doing them and failing.  So rather than be ashamed of them (the natural and powerful response), I should try and celebrate them. So I decided to add a new section to my LinkedIn profile -- right under my work history: Self.Anti-Portfolio.  Projects that didn't work.  I started with things we did at OpenPlans, but have since added to it beyond that. Here's the list so far:

• OpenCore (2005-8) - a platform for organizing/activism. Hugely complex, too much engineering, not enough product/customer focus, trying to be a web service and an open source project at the same time and basically failing at both. (now http://coactivate.org)

• Homefry (2008) - platform for short-term apartment sharing.  Seemed like such a great idea. A few friends and I built a half-functional prototype, but didn't see it through. Maybe a billion dollar mistake. (more here).

• Community Almanac (2009) - platform for sharing stories about local places. Really beautiful, but no one used it (http://communityalmanac.org)

• OpenBlock (2010) - open source fork of everyblock.com, intended for use by traditional news organizations.  Stack was too complicated, and in retrospect it would have been smarter to simply build new, similar tools, rather than directly keep alive that codebase (https://github.com/openplans/openblock)

• Civic Commons Marketplace (2011) - a directory/marketplace of open source apps in use by government. Way overbuilt and never got traction.  Burned the whole budget on data model architecture and engineering.

• Distributed (2014) - crowd funding for tech policy projects. Worked OK, but we discontinued it after brief private pilot.

Looking through this list -- and there are certainly ones I've forgotten, and I will keep adding; trust me -- what I noticed was: in pretty much every one of these cases, the root cause was Big Design Up Front - too much engineering/building, and not enough customer development.  Too much build, not enough hustle.  Another observation is that these were mostly all slow, drawn-out, painful failures, not "fast" failures. I thought I learned these lessons way back in 2006!  That was when I first read Getting Real, which became my bible (pre-The Lean Startup) for running product teams and building an organization.  The ideas in Getting Real were the ones that helped make Streetsblog and Streetfilms such a big success. And they are what helped me understand what was going wrong with the OpenCore project, and ultimately led me to disassemble it and start what became OpenPlans Labs. But it turns out the hard lessons can lurk, no matter how much you think you've taken them to heart.  Perhaps tracking the Anti-Portfolio in public will help.

I had crazy week last week. On Monday, I went to NYC for the day for work, and was overcome by a strange dizzy feeling.  Walls spinning; hard to concentrate; nauseous.  I thought -- maybe I'm just dehydrated. I took a rest during the middle of the day; I drank a lot of fluids.  I made it back to Boston that evening -- barely -- and went straight to bed, assuming all would be clear the next morning. When I woke up, the walls were still spinning, just as they had been.  I started googling.  Now -- it's important to note that I don't have a standard health profile -- 5 years ago, right after our son was born, I discovered that I had several large blood clots, in my intestines and in my head, and I've been seeing hematologists, neurologists, and rheumatologists, and have been on blood thinners, ever since.  As you can imagine, the intersection of "dizziness" and "blood clots" is not a good one. So I headed straight to the ER Tuesday morning, and ended up being scanned, tested, and admitted overnight.  Turns out I did not have a stroke, but rather I have Vertigo caused by an enflamed cranial nerve (likely due to a virus of some kind).  Vertigo is a really strange thing: first, it's amazing how much we take for granted our brain/body's ability to understand and interact with the space around us; when that stops working, it's very distressing.  And second, it's (perhaps even more) amazing how well the brain can adjust, adapt, and re-learn, when certain things stop working the way they had been -- I've been doing PT to re-train my brain, eyes and ears to understand what's moving and what's not moving, and where I am -- and it's been surprisingly effective. But that's not the point of this story.  The point of this story is about how much effort, charm, and determination it takes to get effective medical care -- even in the best case scenario with excellent health insurance, great hospitals, and top doctors. One of the toughest things about last week was getting all of the doctors on the same page with one another. I've got a PCP, a rheumatologist that I used to see in NYC, a history of cat scans and MRIs (from NYC and Boston), a hematologist in Boston -- and now as of last week, a Neurology team in Boston following my case. All of these doctors -- each of whom knows a piece of my story and has expertise to offer -- do not have a way to talk to each other, and their method of sharing information is outdated at best. The result of this situation is a mad scramble.  Trying to get record requests initiated.  Trying to compare new images to old images.  Trying to get the specialists to weigh in with each other or at least communicate at all.  Trying to figure out where the PCP is.  Waiting on hold.  Leaving messages for doctors that don't get returned.  Being scheduled for new cat scans and MRIs that may or may not be necessary -- if only all of the doctors could communicate with one another, and work off of the same set of information. For instance, the day after I was discharged from the hospital -- and we headed to Cape Cod for what remained of our attempted family vacation -- the Neurologist in Boston called and said they noticed something new on the cat scan from two days prior -- and I needed to come back in for another scan.  That meant a 4 hour drive, finding someone to watch the kids (luckily both sets of grandparents were with us), another night away, and another day worrying about what could be.  And it's altogether likely that better communication among doctors -- and easier use of past records -- would have made this unnecessary. Luckily for me, I have a secret weapon.  My wife.  When it comes to medical issues, she has been through a lot -- in particular, a decade of dealing with Chron's disease and Thyroid Cancer.  She has learned -- the hard way -- what it takes to get through the confusion, uncertainty, bureaucracy, under-communication and fear of having a complex medical situation.  She know that you not only need to get connected with the right care at the right time, but you have to be a quarterback, pitbull, and snake-charmer at the same time to get things to happen. In her words, you need to be the sweetest pitbull. Never ever go away or let anyone off the hook, while at the same time, get everyone to like you and care about you. My attitude is a bit different -- I try to avoid being a burden, and tend to assume that people will do their jobs correctly if you let them.  I leave messages. Frannie's approach is different.  On Thursday when we went back for my additional cat scan, we showed up in person at the Hematology unit and the Neuro unit -- unannounced; no appointment.  We tried to make friends with the receptionist (critical).  For a moment, it seemed like she would brush us off, but then she said "well, let me call the head nurse and see if she can come talk to you."  Bingo. The head nurse (an angel if there ever was one) came out and saw us.  Carved out a few minutes to talk.  Mid-sentence, as I was explaining my situation, she ducked out of the room and came back with record requests forms for NYC.  With her other hand, she dialed in the scheduler for the next possible appointment and got me set up. With her other hand, she took down the Neurologist's information so she could coordinate with him. With her other hand, she had NYPH records department on the phone.  With her other hand, she scribbled down her direct line, her pager number, and the Hematologists cell phone number.  She had a lot of hands and she was using them all at once.  Because we were sitting there. When we were done I gave her a huge hug and actually cried a little.  The difference between having a person who knows you, sees you, and can move the gears of medicine for you -- and a person at the end of a phone line or email -- is astounding. And I would never have gotten there were it not for the sweetest pitbull gnawing and smiling our way in. I guess the point of this story is that it shows me how broken the medical system is.  Even in the best case, there is such a lack of communication, coordination and information sharing.  Data is everywhere and nowhere.  Decisions are slower and harder to make than they should be.  Expensive diagnostics are over-used.  Every patient needs their own sweet pitbull to help pry the doors open and get the system to pay attention them and care about them. Thinking about this in terms of apps and data -- it showed me, crystal clear, that there's got to be a better way to do medical collaboration.  What I wanted, throughout all of this, was a simple private chat room for me and my doctors -- all of them -- that provided easy access to my history of records, diagnostics, and care providers, across locations and hospital networks.  A place that let me  -- and them -- ask questions and get answers, and keep everything in one place that everyone could work from.    Of course, there are untold barriers to this vision: insurance, risk/liability, data security.  But it seems obvious to me that that's the future we should be shooting for. In the meantime, we can simply hope to recruit the sweetest pitbulls to have our backs. I know I am super thankful to have mine.

Saying no to things is something I've always been bad at.  I have always been (and to some extent, have prided myself on being) more of a "why not" guy than a "why" guy. This has many of advantages -- I'm open minded and I end up doing tons of interesting things w interesting people.  But it also has some obvious disadvantages -- like feeling overwhelmed, getting behind on things, getting spread too thin, not doing a good enough job on any one thing. I remember reading that one of the cornerstones of Warren Buffet's approach to life is writing up a list of the 10 things you want to do, prioritizing them, then putting the bottom six on a "avoid at all costs" list. And I believe in my heart that the projects / apps / ideas that are tight, focused and well executed are better than the ones that are broadly ambitious and try to boil the ocean. One of my favorite lines, from one of my favorite books is "half, not half-assed". But still, it's hard to say no to things.  Meetings, phone calls, projects, you name it.  It's just hard. But every time I look at my long to do list, or my inbox, or my calendar, and think -- what can I do to be more efficient and effective at doing all of this?  The obvious answer is to just do less.  That's by far the most simple and most impactful approach. How do you save money? Spend less.  How do you save time?  Do less. Easier said than done, but no doubt important.

I can’t claim to be the most disciplined or organized person, but I’m working on both.

I have, however, done a lot to smooth out my moment-to-moment work process, to help me do things more quickly & easily, and to help me avoid distractions where I can.  I can only hope that I win more time using this stuff than I spent setting it up.

So if you’ll indulge this lifehacking moment, here’s my top 5 list of personal productivity tools / hacks:

1) Quicksilver — Quicksilver is a launcher for mac, which gives you a quick keyboard shortcut for jumping to any app.  For example, if I press control-space (to open quicksilver), and then press “p”, it prompts me to open photoshop.  It’s also awesome at remembering your choices and learning from them, so it always presents the thing you want as the first option.  It can do way more than I use it for, but even for what I do (just opening apps), I use it hundreds of times a day and feel lost on a mac without it.

2) Jumpcut — Jumpcut is a clipboard buffer for mac.  In other words, a history for things you’ve copied.  In practice that means I can copy multiple things in a row, without without about which one I need to paste first.  Copy as much as you want, then press command-shift-option-V to cycle through the things you’ve copied and choose what to paste:

3) Quick Compose — this is something I’ve written about before — what I found was that often when I wanted to write an email, I would get distracted as I passed through my inbox on the way.  What I wanted was a way to skip straight to the compose window.  Luckily, this is possible using Quicksilver — I have a “Custom Trigger” set up, so that wherever I am, Command-Shift-M will pop open a new browser window with the gmail compose screen on it.  I use this all day long.

4) Chrome search shortcuts — One of the lesser known features of Chrome (and I believe firefox, and maybe safari too) is the ability to customize your search engines.  Of course, this means setting a default for regular web searches (I use DuckDuckGo), but you can also set up more specialized keyword-based searches.   For example, if I go to the chrome bar, and type in “t nickgrossman”, it will take me to http://twitter.com/nickgrossman — because I’ve set up a custom twitter shortcut with the letter t.  I also have one for Crunchbase, which I use all the time — so I type “c tumblr” to get a quick link to the Tumblr Crunchbase page.  And the one I use the most is the Gmail Search extension, which lets me go directly to searching my email by entering “gs ” in my address bar.  Similar to Quick-Compose, this keeps me out of my inbox when I don’t need to be there. To customize your search queries in chrome, control-click (or right-click on PC) the address bar, and choose “Edit Search Engines…” 5) Jing — I use Jing all day long to take and share screenshots.  I hit command-shift-J and the Jing screenshot grabber pops up. You can then draw on the screenshots if you want, and also post them to share — either to Flickr, email, or FTP (which is what I use, posting them to my own web server) Bonus!) Bookmarklets and Chrome extensions.  Everyone who works with me knows I love these.  So much.  I use them for everything, and have even recently learned how to make my own.  My favorites are:  post to tumblr, post to delicious, add to pocket, add to feedly, send with gmail (maybe my all-time favorite), and many many more (even a few top-secret ones). As I look through these, the obvious theme is “shortcuts”.  Keyboard, chrome button, etc.  I guess really like things that let me go straight to the thing I want to do. And maybe it drives me nuts when I can’t.  I like the fact that the computers I use are hackable / open enough to make this stuff possible, though of course, that is changing.

The past three weeks have been really busy. First a trip to SF with the USV team, then to Austin for SXSW to put on We Heart Wifi, and finally to Iceland where we have been helping establish a new institute for internet policy at Reykjavik University. So as is typically the case, I have fallen behind on everything — email, blogging, seeing my kids… But I am psyched to be back home and to have a few weeks free and clear to recenter and get organized. The busier my life gets, the more I’m impressed with folks who are able to keep their heads above water despite ridiculous schedules and fractured time.  It’s not something I’ve mastered yet, but I’m working on it. For the past two months Frannie and I have been taking yoga, and it’s been incredible.  Totally changes my outlook on everything.  We are lucky to have a really great studio and instructor very close to our house.   Perhaps the thing that has stuck with me the most is the idea that the practice of yoga doesn’t end when the session is over.  That, with practice, you can bring the yoga with you wherever you are, to whatever you’re doing.  Sounds hokey, I know, but it’s pretty profound.   Anyway, the point is: I think there is something in there — about how to keep calm and carry on and stay disciplined when things get hectic.  Easier said than done - but a worthy goal.

Happy MLK Day everyone. I just spent the last half hour reading MLK’s Letter from a Birmingham Jail.  To be totally honest, I don’t think I’ve ever read it in its entirety before.  It is incredibly powerful and moving.  I encourage anyone reading this to take some time with it today. I pulled a few quotes here. King’s letter makes the case — in exceedingly eloquent and persuasive terms — for nonviolent direct action in the face of injustice.  And discusses the historical precedent and moral imperative for distinguishing between just and unjust laws (including a framework for drawing that distinction), and for disobeying unjust laws.  It hammers home the point that we can’t blindly accept “the law” if we don’t take into account the context in which it was created or the morality and justice of the ends it seeks. Part of the beauty of it is the guided tour of the history of changemaking, conflict and progress that Dr. King takes us on — all the way from Socrates, to the Boston Tea Party and the American Revolution, to the Holocaust, to of course the Civil Rights movement.  It’s kind of incredible the extent to which we have to learn and re-learn the dynamics of societal norms and the process by which we arrive at and live under the rule of law.   At the heart of the letter is tension between a moderate “take it slow” approach (embodied at the time by the white southern church, whose leaders the letter was addressed to) and more extreme “force change now” approach (embodied at the time by Elijah Muhammed’s Muslim movement).  King’s articulation of the rationale for a measured and pure — yet intentionally impatient — nonviolent approach is incredibly thoughtful and reasoned. It’s part inspiration and part how-to for anyone working to create positive change in the face of resistance from the status quo. I can’t equate the civil rights movement with the digital rights movement, and I won’t do that here.  But that is the corner of the activism world that I sit in, so it’s the lens that I’m reading this through.  And I can’t help but think about the passing of Aaron Swartz, and the path he charted in the pursuit of social justice, as I read Dr. King’s words.  So many of the conversations I’ve been having this past week have revolved around this question of how we view and respond to acts of civil disobedience. More importantly, I want to use today to reflect on both the (incredible yet entirely incomplete) progress that we’ve been able achieve as a nation since 1963 when this letter was written, and the profound and powerful moral foundation for change that Dr. King’s letter provides.

Sunday night, Cescalouise's iPhone mysteriously went dark.  She had a lot going on Monday, so I gave her my phone to use, then I headed down to NYC for the day and following night. So I’ve been away from home for the last day and a half with no phone.  Not a huge deal, obviously, but also a pretty big departure from normal. What’s interesting is what I’ve missed and what I haven’t missed. Of course, I miss being able to communicate with people from wherever I am — but to be honest I don’t think that’s the thing I miss most.  The biggest thing I miss is the ability to jot down a thought on the fly.  I use Wunderlist and Fetchnotes on a pretty regular basis to capture the passing thought or to-do.  It’s an important part of how I keep my slow hunch going. What I don’t miss is constantly surfing the top of my inbox.  I use android desktop widgets and keep both of my main inboxes on one of my home screens.  Having them there is convenient, and helps me be responsive to email, but it’s bad for focus.  I will probably delete those when I get my phone back. Walking around NYC and riding the subway, my head has been up and I’ve noticed more things (but of course haven’t been able to capture / share them :-)  And of course I notice how many people have their faces in their phones all the time (probably 75% of those of us  waiting for the Amtrak in Boston). All in all, I’m glad to have taken two days off with no phone.   Feels a bit like a cleanse.  I’ll probably do it again.

I love Google Reader. I’ve used it for a long long time now to keep tabs on things.  I suppose it’s an old school method at this point, but I think it’s just great. The screengrab above is one of my home screens on my galaxy s3.  I have moved to a widgets-only mobile desktop, which has become one of my favorite things about the switch from iPhone to Android. Perhaps my favorite part is the way you can “set it and forget it”. When I come across an interesting blog, I save it to one of my reader folder, and then at some point later I get the happy surprise of finding a post from that blog in my feed. Just the other day I figured out how to make reader feeds public.  So here are the ones that I use the most:

• Geek Crush - I’ve been adding to this list for years, and it now has ~100 smart tech folk in it: hackers, thinkers, founders, VCs, etc.

• Net Policy - started earlier this year and now following ~50 people and orgs in the tech policy space.  Pretty great source of news and commentary if you’re into that sort of thing.

• Peer Economy - this one is brand new and far from complete, but I’m working on it. 15 or so blogs following the peer economy space.  What’s that, you ask?  Here’s a hackpad overview and a list of companies - both very early.  

Enjoy!

I always spend a lot of time around the turn of the new year thinking about self-improvement.  This year is no different. Last summer, at a charity fundraiser for a friend, I bought several sessions of personal coaching. Throughout the fall, I’ve been working with my coach, Lisa Lahey, using her methodology called “immunity to change.”  The basic idea is that, given an articulated personal goal you are trying to meet, you may also have a series of “hidden goals” that you don’t realize you’re working towards — and these hidden goals may be in conflict with your positive goals. The resistance inherent in this conflict is our immunity to change. So,  the trick is to identify these hidden goals, then further identify what big assumptions (about yourself or your life)  are behind those hidden goals, and then do a series of experiments to test those assumptions.  Ideally to ultimately prove yourself wrong about the assumptions and vanquish the hidden, constraining goals. For me, the big goal is to close more loops.  One of my worst tendencies is to leave things 80% done (just ask Cescalouse about my home improvement projects).  A big part of my job is to keep momentum going — to close loops and keep energy moving through whatever projects I’m working on.  I can’t become a bottleneck or a place where ideas stagnate and lose energy. One of my hidden, competing goals is that I’m an urgency addict. I tend to procrastinate — ruminating on the size and severity of whatever I’m procrastinating from — until pressures build to such an extent that I am forced to power through in a burst of goal-line adrenaline.  I “get high” from powering through work on a deadline — and I feel the need to get high by a (presumably false) assumption that my stack of work is overwhelming and super human effort is required to get through it.  Unfortunately for me (according to the immunity to change framework), this pattern has been working for me — so the bad behavior is reinforced by a track record of getting things done despite myself.

This is bad for several reasons.  Most importantly: it burns energy needlessly (worrying about things rather than actually doing them), and it reduces collaborative leverage (the more out in front you are on something, the better chance to get external engagement).

So here’s what I’ve been doing to combat my immunity to change: I am consciously shifting my thinking from “big to dos” (i.e., large items on my to do list which are scary and incite procrastination) to “moving the ball forward”.  Given any project on my plate, the new approach is “Ok, I’ll spend an hour and get as much done on {project X} as I can”, rather than “oh man, I really need to {item x}”. Seems like a simple thing, but it actually has been surprisingly powerful.  Yesterday I cut my whole day into hour-long blocks, where I moved the ball forward on each of my big projects for an hour.  It worked.  Items that might have otherwise triggered stress and procrastination dissolve into “getting things done for an hour”.   Moving the ball forward for an hour is progress, no matter how you cut it. In addition to (and perhaps more importantly than) reducing the “looming burden” of a large number of big independent tasks, taking this approach creates focus.  And focus is perhaps the most powerful tool we have (and often the most elusive). This is just a start.  We will see if it sticks.  But I think it is useful and perhaps it can work for others as well.